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Table 23.3 Relative binding affinity of tripeptide aldehydes on thrombin. Arg–H is for the aldehyde that was obtained by reducing the carboxylic acid of arginine. The larger the value of the relative inhibition, the stronger the inhibitor binds to thrombin.

From: Inhibitors of Hydrolases with an Acyl–Enzyme Intermediate

Peptide

Relative inhibition

Gly–Val–Ar–H

1

Gly–Pro–Arg–H

9

Phe–Pro–Arg–H

57

d–Ala–Pro–Arg–H

469

d–Val–Pro–Arg–H

1273

d–Phe–Pro–Arg–H

7370